Methyl p-toluenesulfonate → Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)

HRID 353022Notes

Reaction equation

HRID 353022 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([N+]([O-])=O)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:15][O:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>CCOCC>[C:23]1([CH3:26])[CH:22]=[CH:21][C:20]([S:17]([O-:19])(=[O:16])=[O:18])=[CH:25][CH:24]=1.[CH3:15][N+:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][C:3]=1[S:2][CH3:1]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 3055522-(Methylthio)-6-nitro-1,3-benzothiazole

Product 1

HCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)Yield 63.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6-nitro-2-(methylthio)benzothiazole 7 (0.5 g, 2.2 mmol) and methyl-p-toluenesulfonate (3.7 g, 20 mmol) was heated from 120° C. to 145° C. over one hour. To the cooled solution was added 30 mL of ether. The resulting amorphous solid was triturated with acetone to provide a pale mauve solid (0.57 g, 1.4 mmol, 63%).

Workup

  1. temperaturewas heated from 120° C. to 145° C. over one hour
  2. customThe resulting amorphous solid was triturated with acetone

Sources & evidence

ORD record
ord-4c7b60ccc7c64a35b58b8275ba2bd5b9
Source dataset
uspto-grants-2004_06
Patent number
US06750024B2

Reaction notes

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